One Way

Popular Filters

+ 1 more

Departure Airports

One Way Price

CAD 149 CAD 700

Duration

2 h 35 m 9 h 0 m

Stops From Boston

Departure From Boston

Before 6 AM

CAD 229

6 AM - 12 PM

CAD 149

12 PM - 6 PM

CAD 260

After 6 PM

CAD 281

Arrival at Chicago

6 AM - 12 PM

CAD 149

12 PM - 6 PM

CAD 229

After 6 PM

CAD 281

Alliances & Airlines

Oneworld

(5)

SkyTeam

(4)

Star Alliance

(3)

Layover Airports

Layover Duration

1 h 0 m 4 h 0 m

Top Flights From Chicago

Boston To Chicago Flights

Book Boston to Chicago flight tickets at lowest price. Get best deals on your upcoming Boston to Chicago flights only on MakeMyTrip. Also Book Chicago to Boston Flights. Currently 18 flights flying from Boston to Chicago. To save maximum on flight booking click on below Fare Calendar button and choose your dates.Avail Zero Cancellation for flight bookings.


Sorted By:
Departure
Duration
Arrival
Price
JetBlue Airways

CAD 149

Boston to Chicago , 29 Mar

JetBlue Airways B6 | 311

08:00

Sun, 29 Mar 26

Terminal C

Boston, United States

03 h 10 m

10:10

Sun, 29 Mar 26

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines

CAD 184

Boston to Chicago , 29 Mar

Delta Air Lines DL | 2570

07:25

Sun, 29 Mar 26

Terminal A

Boston, United States

03 h 10 m

09:35

Sun, 29 Mar 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

United Airlines

CAD 196

Boston to Chicago , 29 Mar

United Airlines UA | 1414

06:00

Sun, 29 Mar 26

Terminal B

Boston, United States

02 h 59 m

07:59

Sun, 29 Mar 26

Terminal T1

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines

CAD 229

Boston to Chicago-Midway , 29 Mar

Delta Air Lines DL | 2303

05:50

Sun, 29 Mar 26

Terminal A

Boston, United States

03 h 22 m

08:12

Sun, 29 Mar 26

Terminal T1

Minneapolis, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines DL | 3792

11:49

Sun, 29 Mar 26

Terminal T1

Minneapolis, United States

01 h 36 m

13:25

Sun, 29 Mar 26

Chicago-Midway, United States

BAGGAGE : CHECK INCABIN

Information not available

American Airlines

CAD 230

Boston to Chicago , 29 Mar

American Airlines AA | 1813

09:25

Sun, 29 Mar 26

Terminal B

Boston, United States

02 h 35 m

12:00

Sun, 29 Mar 26

Charlotte, United States

BAGGAGE : CHECK INCABIN

Information not available

American Airlines AA | 2533

15:05

Sun, 29 Mar 26

Charlotte, United States

02 h 16 m

16:21

Sun, 29 Mar 26

Terminal T3

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

American Airlines

CAD 232

Boston to Chicago , 29 Mar

American Airlines AA | 1328

06:52

Sun, 29 Mar 26

Terminal B

Boston, United States

03 h 11 m

09:03

Sun, 29 Mar 26

Terminal T3

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

American Airlines

CAD 246

Boston to Chicago , 29 Mar

American Airlines AA | 1813

09:25

Sun, 29 Mar 26

Terminal B

Boston, United States

02 h 35 m

12:00

Sun, 29 Mar 26

Charlotte, United States

BAGGAGE : CHECK INCABIN

Information not available

American Airlines AA | 2343

13:00

Sun, 29 Mar 26

Charlotte, United States

02 h 16 m

14:16

Sun, 29 Mar 26

Terminal T3

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

American Airlines

CAD 255

Boston to Chicago , 29 Mar

American Airlines AA | 1813

09:25

Sun, 29 Mar 26

Terminal B

Boston, United States

02 h 35 m

12:00

Sun, 29 Mar 26

Charlotte, United States

BAGGAGE : CHECK INCABIN

Information not available

American Airlines AA | 1218

14:05

Sun, 29 Mar 26

Charlotte, United States

02 h 16 m

15:21

Sun, 29 Mar 26

Terminal T3

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

United Airlines

CAD 260

Boston to Chicago , 29 Mar

United Airlines UA | 1732

12:30

Sun, 29 Mar 26

Terminal B

Boston, United States

02 h 59 m

14:29

Sun, 29 Mar 26

Terminal T1

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines

CAD 281

Boston to Chicago , 29 Mar

Delta Air Lines DL | 5858

20:20

Sun, 29 Mar 26

Terminal A

Boston, United States

02 h 56 m

22:16

Sun, 29 Mar 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Chicago Address

Boston Address

Boston to Chicago Flights Information:-

Looking for Boston to Chicago Flight? Here’s all you need to know! For convenience and to save time, pick the airport that is closest to your destination. The nearest airport to Chicago is Chicago Midway Intl and the IATA code for the same is CHI.
Currently, there are 5 airlines operating flights between the two destinations and approximately 18 flights take off from Boston to Chicago every week.

Need information on Boston to Chicago airfare?

The minimum airfare for a Boston to Chicago flight would be 149, which may go up to 680 depending on the route, booking time and availability.
It is recommended that you book a round-trip, since it always works out to be more economical.

Flight Details for Boston to Chicago

If you are looking for Boston to Chicago flights, there is no dearth of options to choose from. Several reputed airlines currently offer both direct and indirect flights between the two destinations. Some of these are American Airlines, Delta Air Lines, JetBlue Airways, Southwest Airlines, United Airlines. Out of these, only 13 airlines operate direct flights. Indirect flights may involve more travel time, but they usually cost lesser than direct flights.

The number of flights operated by each airline is as follows:American Airlines : 5, Delta Air Lines : 5, JetBlue Airways : 5, Southwest Airlines : 5, United Airlines : 5

To board the first Boston to Chicago flight, choose Delta Air Lines, which departs at 05:50 The last flight for this route is Delta Air Lines, departing at 20:20

Chicago Airport Information

Chicago Midway Intl

About Boston (BOS)

Boston is the most famous and largest city in New England, the capital of the state of Massachusetts. The city is one of the most influential, wealthy and historic cities in the United States of America. Its plethora of highly famous museums, attractive historical sites and wealth of live performances, all demonstrate why the city gets over a 16.3 million visitors every year. This makes it one of the ten most famous tourist destinations in the country. The historic ‘City of Boston’ has some of the most fascinating and attractive monuments and tourist attractions in the North-eastern United States. Being rich in traditions makes it a famous tourist location that offers an astonishing dining and sightseeing. Its old town trolley tours offer the most famous sightseeing experience in the city. Some of the major attractions of Boston include Boston Children's Museum, Museum of Fine Arts, Harvard Art Museum, Isabella Stewart Gardner Museum, New England Aquarium, and Semitic Museum and so on. Excellent seafood of Boston is available at the nearby New England coast. Boston has a thriving night-life for all those who are more into night parties and also make it perfect location for having fun with friends. It is known to be a 'drinking' town and bar hopping is extremely easy and commonly done here. Local specialities of the city include baked beans, cod, and clam chowder, so don't forget to taste it. Boston Public Library, Newbury Street, The Christian Science Plaza, Skywalk Observatory, Mary Baker Eddy Library, Boston City Hall, Bunker Hill Monument, Neptune Oyster, Boston Duck Tours and so on are some of the major sightseeing of Boston. You can freely move anywhere in the city as it is well-linked with transport facilities. For air travellers, Boston Logan International Airport is a main gateway to Boston and New England. There are number of leading airlines which provide their regular flight services towards Boston. At MakeMyTrip.com, one can book air ticket online and choose the best deal as per your decided budget. Even you can also do online hotel booking in Boston from MakeMyTrip.com and get huge discounts on it.

About Chicago (CHI)

Chicago is a dazzling city that captivates visitors with its vibrant atmosphere and stunning architecture. For travelers from Canada, Chicago offers an array of experiences, from world-class museums to picturesque waterfront parks. The city's rich cultural heritage and dynamic arts scene make it a must-visit destination.

Best Time to Visit

The ideal time to visit Chicago is during the spring (April to June) and fall (September to November) when the weather is pleasant, and the city is alive with festivals. Summers can be warm and bustling, while winters are cold and snowy, perfect for those who enjoy winter sports.

Getting There

Chicago is served by two major airports: O'Hare International Airport (ORD) and Midway International Airport (MDW). There are numerous flights to Chicago from Canada, including direct flights from Toronto, Vancouver, and Montreal. Ensure you have a valid passport and check visa requirements before booking your flight. Airlines such as Air Canada and United Airlines offer cheap flights to Chicago, making it accessible for Canadian travelers.

Where to Stay

Chicago boasts a wide range of accommodation options to suit all budgets. For luxury, consider staying in the Magnificent Mile area, home to upscale hotels and designer boutiques. Budget travelers can find affordable options in neighborhoods like Lincoln Park and Wicker Park. The Loop, Chicago's downtown area, is ideal for tourists wanting to be close to major attractions.

Must-See Places & Experiences

Chicago is renowned for its iconic landmarks and cultural institutions. Don't miss:
• The Art Institute of Chicago
• Millennium Park and the famous Cloud Gate sculpture
• Navy Pier, offering entertainment and stunning lake views
• Museum Campus, home to the Field Museum, Shedd Aquarium, and Adler Planetarium
• The Magnificent Mile for shopping
• Willis Tower Skydeck for breathtaking city views

Local Transportation

Chicago's public transportation system is efficient and easy to navigate. The Chicago Transit Authority (CTA) operates buses and trains that connect the city and suburbs. Taxis and ride-sharing services like Uber and Lyft are readily available. For a scenic option, consider renting a bike and exploring the city's extensive bike paths.

Food & Dining

Chicago's culinary scene is diverse and delicious. Be sure to try local specialties such as deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches. The city offers a variety of dining options, from Michelin-starred restaurants to casual eateries. Recommended spots include:
• Lou Malnati's Pizzeria for deep-dish pizza
• Portillo's for Chicago-style hot dogs
• Alinea for an upscale dining experience

Practical Travel Tips

• Currency: The US Dollar (USD)
• Language: English
• Safety: Chicago is generally safe, but be aware of your surroundings and avoid less populated areas at night
• Useful Apps: Download the CTA Transit app for public transport information and OpenTable for restaurant reservations

Start planning your trip and book your Chicago flight today. With so much to offer, Chicago is a city that promises unforgettable experiences for Canadian travelers.

Frequently Asked Questions - Boston to Chicago Flights

Is there a way to make flexible departure date bookings for your Boston to Chicago flight tickets?

Some travel portals like MakeMyTrip offer flexible departure and arrival booking option with certain air carrier when booking from Boston to Chicago. You can check the flexible booking flight options once you get the results filters based on your search and make the booking accordingly. Please note, some airlines make charge extra for flexible travel dates.

How do MakeMyTrip finds the lowest available dare for flights from Boston to Chicago?

MakeMyTrip is a popular travel portal that also works as a travel search engine that allows you to see best available results for your flight search. Every time you make search for flights to any destination, the MMT algorithm picks all the available air carriers for the route and filter rates basis on the cheapest fare available in their system. At MMT, you can not only search flights on the basis of the fare, but you can also see which flight offers direct route, which has multiple stop-overs, baggage allowance, in-flight meal options, cancellation policy, etc. You can also check available discounts offered by payments partners and air carriers when booking the flight.

Is passport mandatory to travel from Boston to Chicago?

When making an international trip, passport is mandatory as it defines your identity to the other nation officials. The VISA norms may differ from country to country, which means some would allow Visa on arrival and others may require you to obtain visa in advance. But the availability of passport is mandatory at the time of departure and arrival as well.

Can I cancel my ticket from Boston to Chicago without cancellation charges?

To avoid cancellation charges on your air tickets, you need to make a selection at the time of booking for ZERO cancellation. Please note, the zero cancellation facility is chargeable with minimum amount and can help you save a lot at the time sudden cancellations.

Can I find cheap accommodation near to airport when travelling from Boston to Chicago?

There are several accommodation options available near the Chicago Midway Intl. You can check for both budget friendly and well as five star accommodation near the airport depending on your requirement and budget. These hotels are mostly suitable for business travellers.

Which airlines offer cheapest airfare from Boston to Chicago?

There is no set pricing for airlines to offer cheap flight fare from Boston to Chicago. These fares are mostly decided on the basis of algorithms followed by air carriers to final the prizing based on demand. However, some multiple route flights with stop-overs offer cheap flights as compared to direct flight departing from Boston to Chicago.

What is the best time to book cheap flight tickets from Boston to Chicago?

To get cheap flight tickets from Boston to Chicago, the best time would be to plan your trip during the off season. At that time the flight tickets are usually cheaper than the peak season and the accommodation booking is also available at the affordable price. The other way of booking cheap flight tickets from Boston (BOS) to Chicago (CHI) is to book atleast 4 weeks in advance before your departure date to get competitive pricing on your tickets even during the peak season.